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Substance Name: Scopolamine
RN: 51-34-3
UNII: DL48G20X8X
InChIKey: STECJAGHUSJQJN-FWXGHANASA-N

Note

  • An alkaloid from SOLANACEAE, especially DATURA and SCOPOLIA. Scopolamine and its quaternary derivatives act as antimuscarinics like ATROPINE, but may have more central nervous system effects. Among the many uses are as an anesthetic premedication, in URINARY INCONTINENCE, in MOTION SICKNESS, as an antispasmodic, and as a mydriatic and cycloplegic.

Molecular Formula

  • C17-H21-N-O4

Molecular Weight

  • 303.3559
 

Classification Codes

  • Adjuvants, Anesthesia
  • Autonomic Agents
  • Central Nervous System Agents
  • Cholinergic Agents
  • Cholinergic Antagonists
  • Drug / Therapeutic Agent
  • Human Data
  • Muscarinic Antagonists
  • Mutation Data
  • Mydriatics
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Scopolamine

MeSH Heading

  • Scopolamine hydrobromide

Synonyms

  • (-)-Hyoscine
  • (-)-Scopolamine
  • 1alphaH,5alphaH-Tropan-3alpha-ol, 6beta,7beta-epoxy-, (-)-tropate (ester)
  • 3-Oxa-9-azatricyclo(3.3.1.0(sup 2,4))nonan-7-ol, 9-methyl-, tropate (ester)
  • 3-Oxa-9-azatricyclo(3.3.1.O(sup 2,4))nonan-7-ol, 9-methyl-, tropate (ester)
  • 6,7-Epoxytropine tropate
  • 6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate
  • 6beta,7beta-Epoxy-1alpha,5alpha-tropan-3alpha-ol
  • 6beta,7beta-Epoxy-3alpha-tropanyl S-(-)-tropate
  • alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester
  • Atrochin
  • Atroquin
  • Boro-Scopol
  • EC 200-090-3
  • EINECS 200-090-3
  • Epoxytropine tropate
  • HSDB 4074
  • Hydrobromicum, Scopolaminum
  • Hyoscine
  • Hyosol
  • Isopto Hyoscine
  • l-Scopolamine
  • Oscine
  • Scopace
  • Scopine (-)-tropate
  • Scopine tropate
  • SEE
  • Skopolamin
  • Transderm SCOP
  • Transderm-Scop
  • Tropic acid, 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(sup 2,4))non-7-yl ester
  • Tropic acid, ester with scopine
  • UNII-DL48G20X8X

Systematic Names

  • Benzeneacetic acid, alpha-(hydroxymethyl)-, (1alpha,2beta,4beta,5alpha,7beta)-9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (alphaS)-
  • Benzeneacetic acid, alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (7(S)-(1alpha,2beta,4beta,5alpha,7beta))-
  • Hyoscine
  • Scopolamine

Registry Numbers

CAS Registry Number

  • 51-34-3

FDA UNII

  • DL48G20X8X

Other Registry Numbers

  • 14797-94-5
  • 226562-00-1
  • 28901-63-5
  • 58670-87-4
  • 65319-33-7
  • 97991-84-9

System Generated Number

  • 0000051343

Structure Descriptors

InChI

1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1

InChIKey

STECJAGHUSJQJN-FWXGHANASA-N

Smiles

CN1[C@@H]2C[C@H](C[C@H]1[C@H]3[C@@H]2O3)OC(=O)[C@H](CO)c4ccccc4

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intramuscular 4ug/kg (0.004mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
"Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents," National Research Council, 3 vols., Washington, DC, National Academy Press, 1982-85Vol. 1, Pg. L1, 1982.
human TDLo subcutaneous 2ug/kg (0.002mg/kg) BEHAVIORAL: EXCITEMENT

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Journal of Pharmacology and Experimental Therapeutics. Vol. 137, Pg. 133, 1962.
man TDLo intramuscular 24ug/kg (0.024mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 32, Pg. 250, 1973.
man TDLo subcutaneous 14ug/kg (0.014mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
American Journal of Psychiatry. Vol. 141, Pg. 1010, 1984.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: IRRITABILITY

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 1727, 1971.
mouse LD50 intravenous 100mg/kg (100mg/kg)   Journal of Medicinal Chemistry. Vol. 26, Pg. 1772, 1983.
mouse LD50 oral 1275mg/kg (1275mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: TREMOR
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 134, Pg. 255, 1961.
mouse LD50 subcutaneous 1700mg/kg (1700mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 56, Pg. 85, 1936.
rabbit LDLo intravenous 50mg/kg (50mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rabbit LDLo subcutaneous 75mg/kg (75mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 oral 2650mg/kg (2650mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C272, 1991.
women TDLo subcutaneous 13ug/kg (0.013mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
American Journal of Psychiatry. Vol. 141, Pg. 1010, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 59 deg C   EXP
pKa Dissociation Constant 7.75 (none) 25 EXP
log P (octanol-water) 0.98 (none)   EXP
Water Solubility 1.00E+05 mg/L   EXP
Vapor Pressure 7.18E-09 mm Hg 25 EST
Henry's Law Constant 3.36E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.97E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.